No to get Debby finished, I.E. blackmail her into not messing with Angel, you have to have done the Tennis scene, and to get Sophie to agree to help you with that, you have to finish her arc and have sex with her. To have sex with her, you have to have finished Ashley's arc. There should not be any other way to do this. At least that's how it played out for me, I had to put off Debby for over a month to get Sophie along far enough with all of her grinding, before I could think about getting her to help me with Debby, and even then, it took two tries, because he had to go through it again, AFTER having the idea, before he thinks of the idea he already had in the hints, so it takes one more day there too. You should not be able to do these things out of order...